What property management software or tools would you recommend for tracking rent payments, leases, and maintenance requests?

We use a third party servicer to do all of this - much easier and when starting just tracked payments in wuickbooks as servicer tracked everything else 

Unlike some buyers, I ALWAYS go look at the properties before the sale and discovered that the vacant lot had an active railroad track on it and therefore was unbuildable, and would remain unbuildable until the railroad removed their track. 

Being clear about what you want to do from the start not only helps you stay on track, but it also makes it easier to spot problems or delays before they happen.I totally agree that talking to people is important.

My belief is that if you can find a good enough deal, you can make it work - even with limited track record.

Legal violations and penalities(fines) even if you have accounting software to track the difference. 

So I committed to tracking everything throughout the year.

Right now, you may be looking at it as scalable, but assembling a team without a track record is hard because some may end up being leeches.

The other thing could be tracking what you have had come up on the last 5-10 projects after closing, i.e. the water heater was at the end of life when we bought the last 6 out of the last 10 properties.

If entities are disregarded, you can keep up with more than 1 in a single QBO account using the location/business feature to keep track of them separately.